(-)-Benzyl 2,3-dide-oxy-β-d-erythro-hex-2-eno-pyran-oside.

Shigeru Ohba,Yuji Ueda,Takeshi Sugai,Kengo Hanaya,Hayato Okazaki,Mitsuru Shoji

doi:10.1107/s1600536813031140

Shigeru Ohba, Yuji Ueda + Show 4 more

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https://doi.org/10.1107/s1600536813031140

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Abstract

In the title compound, C13H16O4, the six-membered ring of the sugar moiety shows a half-chair conformation. In the crystal, molecules are connected via O—H⋯O hydrogen bonds, forming columns around twofold screw axes along the b-axis direction. There is a disorder of the benzyloxy group, which has two possible orientations with the phenyl group lying on a common plane [site-occupancy factors = 0.589 (9) and 0.411 (9)].

Highlights

Introduction of methylsulfonyl group on freeC4—OH (1c) and subsequent nuleophilic attack with benzyl alcohol provided the title compound, (I)(81%).In the present study, the regio- and stereochemistry of (I) has been determined, there is a complicated disorder.The benzyloxy group has two possible orientations, O4A/C11A—C17A and O4B/C11B—C17B, and their site occupation sup-1 supporting information factors are 58.9 (9) and 41.1 (9)%, respectively
There is a disorder of the benzyloxy group, which has two possible orientations with the phenyl group lying on a common plane [site-occupancy factors = 0.589 (9) and
The C10—O4A and C10—O4B bond directions make an angle of Molecular structure of the title compound with anisotropic displacement parameters drawn at the 30% probability level

Summary

Structure Reports

Hanaya,b Mitsuru Shojib and Takeshi Sugaib a Research and Education Center for Natural Sciences, Keio University, Hiyoshi 4-1-1, Kohoku-ku, Yokohama 223-8521, Japan, and bDepartment of Pharmaceutical. Key indicators: single-crystal X-ray study; T = 292 K; mean (C–C) = 0.009 Å; disorder in main residue; R factor = 0.056; wR factor = 0.255; data-to-parameter ratio = 8.2. There is a disorder of the benzyloxy group, which has two possible orientations with the phenyl group lying on a common plane [site-occupancy factors = 0.589 (9) and. Data collection: WinAFC Diffractometer Control Software (Rigaku, 1999); cell refinement: WinAFC Diffractometer Control. Software (Rigaku, 1999); data reduction: CrystalStructure (Rigaku, 2010); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: CrystalStructure (Rigaku, 2010)

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